The Perfect Walking Tours of Boston With Food and Drinks Along the Way

Boston’s manageable size has always made it one of the most walkable cities in America. The famous 1990s Big Dig project, which sank the city’s major highways underground and replaced them with pedestrian greenways, has made it even friendlier for those on foot.

The following three journeys will take you along some of Boston’s most essential walking routes. Any of them can be done separately on low-key afternoons, or connect all three to get your steps in for the week and see everything the city has to offer.

Walk one: Brownstones and Green Monsters

This 2.5-mile (four-kilometer) walk will take you through some of Boston’s cultural high points – from the hip and historic South End and the Museum of Fine Arts to Fenway Park.

Shops in the South End

Start at South End Buttery, and grab a coffee and a croissant while you lace up your walking shoes. Sip your coffee as you take a lap around the block, stopping into PATCH NYC and Lekker Home – two of Boston’s best interior-design shops – to get a sense of the South End’s hip and high-ticket aesthetic.

Brownstone browsing

Now head up tree-lined Union Park Street towards Tremont Street, which will take you through a leafy neighborhood lined with immaculate (and expensive) brownstones. Hang a left on Tremont Street and give yourself some time to meander through dozens of independent shops on this stretch, including SAULT New England for sharp men’s clothing. Feel free to zigzag around the sidestreets here – you’ll get a feel for the historical charm and catch a glimpse of some modern construction straight out of Dwell magazine.

The Pond at the Pru

Eventually, take a right on West Newton Street to head towards the Christian Science Plaza, an IM Pei-designed public space that surrounds the headquarters of the Christian Science church next to the Prudential Center. The long reflecting pool is an impressive counterpoint to the towering skyscrapers that crowd the skyline just behind it.

From here, cut through the plaza and hang a right on Massachusetts Avenue. Whether you’re a sneakerhead or not, it’s worth popping into Bodega. Behind a false soda machine in this unassuming convenience store hides a high-concept streetwear shop specializing in limited-edition Nikes and other gear. If you’re hungry, grab some authentic Thai and Vietnamese food across the street at Pho Basil. This place will have a line out the door by 5pm, so it’s best to go early.

Trees in the Fens and art at the MFA

Having caught your second wind, walk through the lush Back Bay Fens to the Museum of Fine Arts. While its world-class permanent collection shines, the museum’s multimedia special exhibitions have recently taken it to another level.

Fenway franks at Fenway Park

By now, you’re feeling sufficiently highbrow, but don’t forget that Boston is also a sports town. Even if you don’t know Mookie Betts from Mo Vaughn, it’s hard not to feel chills the first time you see the famous green walls of Fenway Park rising above Kenmore Square. A Red Sox game is one of the great experiences in Boston – you can typically snag affordable tickets on the day of a game on the secondary market. For dinner, grab yourself a Fenway Frank (vegetarian available) and an ice-cold beer, and embrace America’s pastime.

Walk two: Boston’s green spaces

This three-mile (4.8-kilometer) walk will take you through Boston’s renowned parks, from Fenway to the Charles River Esplanade. And don’t worry if you’re not an Eagle Scout; there’s time to stop for a breakfast sandwich and a beer along the way.

Stroll around Fenway

Even during the off-season, Fenway Park is a sight to see. You can schedule a tour of the ballpark during quiet times or just walk around. Take a couple of photos near the Green Monster, and grab some Sox souvenirs for the Yankees fans in your life. Then hop on Ipswich Street, which acts as a concourse between Fenway and the Back Bay neighborhood.

Grub and tunes

Morning or afternoon, visit Pavement Coffeehouse for its in-house roasted coffee, and stay for its home-made bagels. Treat yourself to Pavement’s flagship ‘Sunrise’ breakfast sandwich, available with bacon, sausage or tempeh. As you exit, be on the lookout for street musicians (buskers) – you’re right in the middle of Berklee College of Music. St Vincent, Passion Pit, John Mayer, Gillian Welch and Rivers Cuomo all studied music here, so you never know which future rock star you might see.

Trendy Newbury and greenery on Commonwealth Avenue

Head over to Newbury Street to check out Boston’s premier shopping strip. Trident Booksellers and Café is a great place to browse for the perfect novel, and Newbury Comics has an excellent selection of vinyl LPs in its basement.

Once you’ve tired of navigating the crowds of shoppers, cut over to Commonwealth Avenue, Boston’s most stately avenue and the perfect counterpoint to the bustle of Newbury Street. Here, you’ll find a pedestrian-only, tree-lined mall (a walking mall, not shopping mall) stretching to Boston Common. Along the way, you’ll find monuments to Boston’s unsung heroes, from abolitionists to firefighters, educators to suffragists. If you’re in the city during the spring or autumn, be ready for an abundance of blossoms or fiery leaves.

At the end of the mall, you’ll find yourself at the bronzed feet of George Washington, or rather his horse, which stands at the entrance to the Boston Public Garden. These European-style gardens are immaculately maintained, considering the volume of people who pour through every day. The scenery here – manicured flowers and greenery surrounded by modern skyscrapers – is worth a trip alone, but many people visit to ride the Swan Boats. If you want to skip the ride, opt for a photo from the footbridge.

Historic Beacon Hill

For more quintessential Boston photo ops, cut through Boston Common to the picturesque Beacon Hill neighborhood. Head up Charles Street past the shops and pubs and go to Louisburg Square, whose red-brick row houses will make you feel as though you’re living in Revolutionary-era Boston.

River views on the Esplanade

Cross the footbridge at the end of Charles Street to go to the Charles River Esplanade, a stretch of parkland that runs alongside the Charles River, which separates Cambridge from Boston. If all this walking has made you thirsty, you’re in luck. The Owl’s Nest beer garden (run by Boston craft-beer juggernaut Night Shift) serves ice-cold IPAs, saisons and other refreshments right on the river from May through September.

Walk the bridge to the Massachusetts Institute of Technology (MIT)

For a fun side trip, cross over the Longfellow Bridge, which connects Boston to Cambridge. About halfway across the bridge, turn to your left for a postcard view of Boston, with the river in the foreground and the city’s skyline in the background. Just over the bridge, you’ll be standing on the MIT campus. Its mix of modern buildings is a purposeful counterpoint to Harvard’s red-brick traditionalism, with no better illustration than the Stata Center, Frank Gehry’s trippy academic building.

Walk three: Beyond the Freedom Trail

This three-mile (4.8-kilometer) walk will take you through the touristic heart of Boston along the Freedom Trail and North End, ending at an 18th-century pub where George Washington and Paul Revere got their drink on.

Towers and tombstones

Start at Boston Common, the city’s central park, grabbing a coffee or tea for your journey at Thinking Cup. Look for the towering steeple of Park Street Church and head in its direction on Tremont Street, passing the Granary Burial Ground where many Revolutionary War luminaries, from Paul Revere to Samuel Adams, are buried. On your right, you’ll see the Omni Parker House, where JFK is said to have proposed to Jackie Bouvier back in the day.

Civic fights and civil rights

Hang a right on School Street and a left on Washington Street to approach the Old State House. This red-brick beauty is one of the oldest buildings in the US and the site of many formative events for the city and country, including the Boston Massacre. Cross the street to Boston’s City Hall Plaza and high-five the statue of Bill Russell, Presidential Medal of Freedom recipient for his leadership in the Civil Rights Movement and peerless NBA legend who brought home 11 championships with the Celtics. As you descend the steps from City Hall Plaza and cross the street, pause for a moment at the moving New England Holocaust Memorial.

Traditional and local foods

By this point, you may be ready for a break from the historic sites. If you’d rather skip eating at the quaint but touristy Union Oyster House and Faneuil Hall Food Market, go to Boston Public Market instead. Here, you’ll find an array of artisanal food kiosks from around the state, including coffee, donuts, pastrami sandwiches and banh mi.

Harborwalk

Walk off your lunch with a stroll along Boston Harbor on the gorgeous Harborwalk. This waterfront trail runs for 47 miles (76 kilometers) along the Massachusetts waterfront. From the Public Market, take Hanover Street towards Christopher Columbus Waterfront Park – some of the best views are at the ends of the piers here. If your time is limited, make sure to walk around the perimeter of the New England Aquarium (no admission required), where you’ll have incredible harbor views, as well as views of the aquarium’s resident seals.

The next stretch will take you through Boston’s historic North End, legendary for the multitude of homey Italian restaurants and cafés lining Hanover Street. Mike’s Pastry attracts the crowds, but Caffé Vittoria next door has a better ambience for a mid-afternoon pastry or coffee. Follow Hanover Street until you see the Paul Revere statue on your left – cut through this park and have a look at the Old North Church, where the whole “one if by land, two if by sea” scenario supposedly went down.

Celebrate the Revolution with a beer

Walking over the Washington Street footbridge will give you time to brush up on your bad Boston accent because you’re heading to Charlestown, a favored movie backdrop for Ben Affleck and Matt Damon. Give yourself some time to walk around the piers of the Charlestown Navy Yard, a decommissioned naval base with great harbor views and moored wooden battleships. Pass by the Bunker Hill Monument, this neighborhood’s talisman, on your way to a much-deserved pint at the atmospheric 18th-century pub The Warren Tavern.